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Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose

Cox, Liam R and DeBoos, Gareth A and Fullbrook, Jeremy J and Percy, Jonathan and Spencer, Neil S and Tolley, Malcolm (2003) Catalytic asymmetric synthesis of a 1-deoxy-1,1-difluoro-D-xylulose. Organic Letters, 5 (3). pp. 337-339. ISSN 1523-7060

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Abstract

A new route, of potential strategic importance, to a difluorosugar analogue has been developed. Key steps included a Stille coupling and a highly regio- and enantioselective dihydroxylation of a highly substituted diene. Protecting groups were chosen to enhance the reactivity of the disubstituted allylic fragment in the AD reaction and allow deprotection under orthogonal conditions.